February 28, 2025      —–     Chart #287

Hello Music Friends,

Hey folks, welcome to another edition of Chart of the Week. Some songs don’t just tell a story—they drop you right into the middle of one, like you’re sitting at the counter in some no-name Texas diner, sipping burnt coffee, listening to some old guy tell you about the best damn adventure you’ll never have.

That’s exactly what Guy Clark did with “Desperados Waiting for a Train.”

This one isn’t just a song—it’s a mini-Western epic wrapped up in under five minutes. It’s about growing up around an old-school, hard-living, poker-playing, whiskey-drinking, oil-rig-working surrogate grandfather who was a legend in his own mind and a hero in a young boy’s eyes. There’s a line in there about playing Moon and Forty-Two, and if you don’t know what those are, you probably grew up somewhere with snow.

Clark wrote the song in 1973, and it first appeared on his 1975 album Old No. 1—which, despite its name, was not a whiskey label, though it probably should have been. Like most of Guy Clark’s songs, it was autobiographical, based on his relationship with Jack Prigg, an old wildcatter who probably could’ve won a bar fight against the entire cast of Lonesome Dove.

But like any great song, this one has been covered by some absolute heavyweights over the years.

The Versions You Need to Hear

• Jerry Jeff Walker—The original honky-tonk outlaw gave it a real Texas roadhouse feel in 1973, back when all the best music was made on worn-out Martin guitars and bad decisions.
• David Allan Coe—He recorded it in 1977, because of course he did. Coe could find the sadness in a turkey sandwich, and this song was right in his wheelhouse. CLICK HERE
• The Highwaymen—This Mount Rushmore of country music (Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash) put out what’s probably the most famous version in 1985. When you get that much outlaw country royalty in one room, the only thing left to do is play the damn song and let the magic happen. It’s got a little more polish, a little more drive, but still keeps the song’s heart and soul intact. CLICK HERE
• Slim Pickens in a John Ford Movie—Okay, this version doesn’t exist, but it should, because this song is basically the soundtrack to every dusty, whiskey-soaked Western you’ve ever loved.

The Legacy

What makes “Desperados Waiting for a Train” special isn’t just that it’s a beautifully crafted song—it’s that it feels real. It’s about time, friendship, and watching the people you love slowly fade into legend. It’s about realizing that we’re all just outlaws waiting on our own train to come rolling through.

And if that doesn’t make you want to grab a glass of something brown and strum your guitar a little slower tonight, I don’t know what will.

Here’s the Guy Clark original: Watch here
And the Highwaymen’s classic take: Watch here

Until next time—keep your boots dusty, your whiskey neat, and your guitar in tune.

Keep Rockin’,

Stan Bradshaw